Application of the LADA Strategy for the Synthesis of Unnatural Amino Acids through 1,2-Aryl Migration of Allylic Alcohols

Pannan Miao; Mengyao Zhang; Zhuojun Ni; Qi Chen; Zhankui Sun

doi:10.1021/acs.joc.3c02173

Application of the LADA Strategy for the Synthesis of Unnatural Amino Acids through 1,2-Aryl Migration of Allylic Alcohols

J Org Chem. 2024 Feb 2;89(3):1543-1551. doi: 10.1021/acs.joc.3c02173. Epub 2024 Jan 22.

Authors

Pannan Miao^{1

2

3}, Mengyao Zhang^{1

2

3}, Zhuojun Ni^{1

2

3}, Qi Chen^{1

2

3}, Zhankui Sun^{1

2

3}

Affiliations

¹ Shanghai Frontiers Science Center for Drug Target Identification and Drug Delivery, School of Pharmaceutical Sciences, Shanghai Jiao Tong University, Shanghai 200240, China.
² Engineering Research Center of Cell and Therapeutic Antibody, Ministry of Education, School of Pharmaceutical Sciences, Shanghai Jiao Tong University, Shanghai 200240, China.
³ Zhangjiang Institute for Advanced Study, Shanghai Jiao Tong University, Shanghai 201203, China.

PMID: 38252620
DOI: 10.1021/acs.joc.3c02173

Abstract

Unnatural amino acids are versatile building blocks. Herein, we report the application of the LADA strategy for the direct synthesis of unnatural amino acids through 1,2-aryl migration of allylic alcohols. This reaction proceeds under mild conditions, tolerates diverse functionalities, and works smoothly on different thiols.